My North Brooklyn musical weekend started off on Thursday night with a heavy wave of nostalgia, listening through McCarren Park’s chain link fence as Wolf Parade played songs from 2005’s Apologies to the Queen Mary on the Fest’s main stage. We opted to boogie only in passing so we could make it on time to one of most hyped shows of the Festival, Steve Gunn’s record release at the Music Hall of Williamsburg. I was skeptical at first of his opener, Yonatan Gat, but soon fell into the fuzz-heavy “psych-punk” groove, a fitting introduction to Gunn’s extensive, intricate jams. But though Gunn borrows elements from the jam band format, his pieces are carefully constructed and hypnotic in their cyclical ebbs and flows. His gravely, gasped vocals flit in and out of the sonic whirlpool, but never overpower the rest of his group, the Outliners, most notably the plaintive cry of the pedal steel. Gunn is a bashful front man- “be nice to us,” he exhorted – but a devastating presence when onstage solo. He stepped out armed with only an acoustic guitar for a heartbreaking rendition of “Wildwood” from his 2014 album, Way Out Weather.

Sidebar: Since my press pass afforded me access to the Content and Innovation portions of the week long Festival, which clearly models itself to an extent on Austin’s SXSW, I felt I would be remiss if I didn’t stop by at least one event. Daytime talks clashed with a 9-5 schedule, but from a few friendly conversations (with people who quickly realized I wasn’t anyone glamorous to #network with), I gleaned that many brand consulting firms and digital marketing agencies send their employees to soak up the knowledge and hand out business cards. For a while, I sat in on the panel on “The Year of Women Breaking the Internet,” with speakers from Lenny Letter and Giant Spoon, but quickly realized that this wasn’t a fluff symposium- they jumped headfirst into the nitty gritty of the industry and, jargon lost on me, I ducked out. Drawing moguls from Amazon, GE and Condé Nast this year alone, if Northside can continue to mine the rich landscape of New York City’s tech and marketing fields, it stands to grow exponentially as a dynamic assertion of Gotham as a critical hub of innovation.

Friday night’s McCarren Park lineup featured Kweku Collins, a promising young rapper from Chicago who spits slow, stoner rhymes reminiscent of Kid Cudi. “Stupid Roses” is a catchy, summertime anthem for those frustrated in love. Grandmaster Flash followed, opening with a remix of Prince’s “When Doves Cry,” also paying tribute to both David Bowie (“Under Pressure”) and A Tribe Called Quest’s “genius,” Phife Dog (“Can You Kick It” and “Bonita Applebum”), before his set was through. The legendary DJ was one of the highlights of the weekend, delivering on his promise to play an “authentic DJ set,” which, he explained, meant covering all the genres– from rap to salsa to indie and beyond. From Drake and Bob Marley to- wait for it- “Tom’s Diner” by Suzanne Vega. He educated as he kept the crowd moving, showing off his famous scratches and making a pointed dig at today’s “one song” incarnation of the DJ. Though he didn’t call out EDM by name (“If you’re a DJ, all you need is a laptop, some talent and one track,” Zac Efron boasts in the trailer to the terrible but unfortunately zeitgeisty We Are Your Friends), he did say that such a repetitive format “wasn’t the way [he] intended it,” a humble brag meant to remind any young upstarts in the audience that he was there when hip-hop was born.

Next, we headed back to the Music Hall of Williamsburg for JEFF the Brotherhood, an impressively noisy, grunge-punk two piece, who play kind of music that makes you want to get drunk on beer, commit a misdemeanor and then post your mug shot to Instagram. They’re two millennial miscreants having a blast, and it’s infectious.

Though my pal with a music badge and I were almost turned away at the door of Baby’s All Right at 1 am because of the inconsistent issue of badge capacity (the sway of a badge seems to mean entirely different things from venue to venue), we eventually wore down the gatekeeper and made it in to see Colleen Green. Somehow this skinny girl in big sunglasses, armed with a bass that only serves to pronounce her diminutive stature, delivered — solo — one of the rowdiest, most exciting shows of the fest. She combines razor sharp lyrics about the trials of modern relationships, driving basslines that recall the feel good alt-pop of the aughts and simple melodies carried in pointed, breathy vocals into one hell of a package. Her slick, spooky version of “I Will Follow Him” put an unforgettable feminist spin on the girl-band staple by literalizing it; she peered out from behind dark shades and promised to forever stalk her prey. After soliciting the audience for a glass of Jameson, she invited people to get up on stage and rock out with her, a restrained and amusing spectacle of hair flipping and head bobbing.

Saturday night, Kacey Musgraves added a touch of country to the line-up, doubling down on Northside’s endearing but sometimes perplexing commitment to delivering a diverse line-up. Afterwards, we ran into more trouble with our badges, told at Brooklyn Bowl, despite being plenty early for King Kahn’s set, that they were at capacity; we could pay the $20 cover or leave. But there was plenty else to see, so we hopped over once more to the Music Hall of Williamsburg, where Psychic Ills indulged in a theatrical, psychedelic set, starting in the dark with their big band – which included two backup singers – and sending incense wafting into the crowd. The lead singer’s wife, Liza Thorne, joined the band to sing Hope Sandoval’s part on “I Don’t Mind,” from the group’s just released album, Inner Journey Out.

On Sunday, I caught most of Spanish indie-rockers Hinds’ set from the line to get in, but thankfully the teenage outfit sent waves of lo-fi, guitar-driven girl-power rippling throughout all of North Brooklyn. Next, Rostam Batmanglij made his solo stage debut as ROSTAM. The former Vampire Weekend member (and co-songwriter) has been quietly releasing music for several years through solo projects and with his group Discovery; “You didn’t know those songs, no one has ever heard those songs,” he confessed somewhat self-deprecatingly after his first couple of pieces. “So think of it as a cool thing.” Backed by a string quartet, he showed off his soaring, electro-pop compositions. First, he brought out Wes Miles from Ra Ra Riot (he recently collaborated on the group’s single, “Water”) and to my delight, played “It’s Not My Fault,” a song from their 2009 project, Discovery. They also sang “Gravity Don’t Pull Me,” backed by the same dancers featured in the single’s video. Continuing the wave of guest appearances, Hamilton Leithauser and Angel Deradoorian  joined him for a song from a “forthcoming record he can’t say much about.” Proving the downside of scheduling disparate acts back to back (a common problem at big festivals; remind me to tell you about the Bob Dylan/Lil Wayne fiasco sometime), Brian Wilson fans were already beginning to crowd the stage, and showed little interest in his opener, though ROSTAM’s divine ear for melody stems from the same well of musical genius Wilson sips from, to be sure.

As we retreated from the stage to grab a bite from the food trucks lining the blacktop (or another free sample of Jack Link’s Beef Jerky) before Brian Wilson took the stage, a snippet of conversation changed not only my evening, but colored the way I will forever reflect back on the Northside, my “where were you when” for the worst mass shooting in United States history. Upset because of the lengthy line for the fenced off beer garden, a man snapped at a guard; “there are so many rules!” I turned to roll my eyes in commiseration- we had been body-searched, we had waited in long lines, were frustrated about badge access, we were ready to complain.

Calmly, the guard replied, “we’re trying to avoid another Orlando. We’re trying to keep you safe.”

What a stark reminder that it is a privilege to have entertainment in spades, to spend a weekend roaming around a neighborhood filled with music and food and alcohol, talk and dancing and laughter. It hit me– in a city like New York, a bastion of 24 hour entertainment, perhaps the most important thing we can do is forget about being cool, stop complaining about the details, stop standing in the back with our arms crossed.

With a roster of artists that ran the gamut of age, gender, race and genre, Northside asked Festgoers, will you mosh to JEFF the Brotherhood?; will you put your hands in the air for Grandmaster Flash?; will you sing along to that song you loved in middle school?; will you admit that your dad used to hum that tune when you were a kid? When the chords for “I Get Around” picked up, all posture fell away, and a hipster mecca turned into something else. It transformed into a joyous celebration of nostalgia and sincerity and– corny as it may sound—the simple freedom of music. By the end of the night, I’m happy to report, most all of us chose to be a fan.

-Emily Gawlak